15 High Caliber Interview Questions to Ignite Your Hiring Process

I've done close to 4,000 interviews over the past 10 years.

And I've learned how to be great at them: over the past 6 months, Almanac saw a 90% close rate as we we quadrupled our team.

It's an obvious truth that hiring is remarkably difficult—especially in technology, where your people are essentially your product.

So if you can figure out how to hire, you can figure out how to build great products and great businesses.

Here are some non-obvious, hard-won tips for running an insanely great interview process to find the perfect people for your business.

4 critical tips to follow throughout the interview process
        

#1 Do not proceed without a precise, thoughtful job description.

Don't just quickly copy a generic JD to rush your process forward—invest the time to detail what specific skills and experiences a candidate needs to be successful. Be precise here, if everyone is a fit, then no one is.

A good JD can help your team focus on sourcing and identifying exceptional candidates—because if you don't know the makeup of your ideal candidate, then how will anyone else? Using a great JD to guide your process will generate fewer qualified candidates up front, but it will pay off through a high conversion rate at offer time.

#2 Test for things that can't be taught.

Resumes can tell you about a candidate's experience and technical skills, but you should be focusing on intrinsic skills—things you can't teach someone. In an interview, use your time together to test for the intangibles. Don't waste it going over what you've already read.

#3 Screen for alignment and fit.

Everybody is good at something, and there are plenty of intelligent people in the world. Probing for generic ideals like "intelligence" or "collaboration" or "good communication" is lazy. Instead, look for specific alignment and fit with what your team needs at this moment, and screen for those by designing questions with two things in mind: your company's virtues and position-level specifics.

#4 Focus on understanding the "who."

Finally, look beyond a candidate's skills to who they really are as a human. Get to know them—how they came to be, what drives them, and how they want to learn and grow moving forward. Build a relationship. This could be your next teammate!

15 illuminating interview questions to ask candidates
        

Question #0: What questions do you have for me?

I don't start interviews with a question at all. Rather, I spend the first ten or fifteen minutes of the interview exclusively answering their questions. The quantity and quality of their questions will show me if they've really thought about our company, mission, and the position at hand. It also creates an atmosphere of generosity and reciprocity that makes candidates feel comfortable and heard.

Question #1: What is your superpower?

After about 15 minutes, now the actual interview starts. I love opening by probing about their self-perceived strengths. But rather than ask them a question that leads to generic answers, asking a candidate about what makes them exceptional forces them to think about what truly defines them professionally and personally. It also also helps candidates feel seen and appreciated, generating positive momentum for the harder questions to come.

Great answers here demonstrate confident self-awareness and create a memorable frame for you as the interviewer later on.

Question #2: If I interviewed your sibling(s) and three best friends and asked them to describe you, what three words would they use?

This helps me to understand their personality more specifically I invite them to speak on behalf of those closest to them because it forces them to provide an honest answer—candidates wouldn't want to misrepresent their friends and family's perspective!

Question #3: What's the name of your current manager? If I asked them what you do exceptionally well compared to others, what would they say?

Research shows that when people are asked about their own contributions, they tend to overestimate their impact. However, when asked to answer on behalf of another person—say, their manager—they tend to remove their own biases and estimate more truthfully. There's also a bit of accountability baked into the question as most managers are only a phone call away.

My favorite answers here are when candidates say, "Oh, I chatted about this with my manager just last week." It's a flag when candidates talk poorly about their manager or become defensive

Question #4: What would your manager say are your greatest areas for improvement?

Again, I phrase the question in a way that forces the candidate to remove their own bias and share a vulnerable truth. Candidates often know this question is coming, but this frame often reveals a deeper truth than they might have prepared beforehand.

Great responses share an actual weakness, not just "I work really hard" or "I love making things perfect." Sharing true areas for development shows the candidate is mature enough to reveal a flaw, knowing that they have enough strengths to outweigh it.

Question #5: What would your manager say are your weakest hard skills?

I go for the jugular here by asking about not a personality-based flaw, but some technical part of their current job at which they're not great. People are not used to being asked so directly where they could be better, and great candidates are honest and candid here. I use their answers to directly evaluate their potential for impact and effectiveness in the role for which they've applied.

Question #6: What are your biggest professional pet peeves?

By asking about "pet peeves", candidates can be open and honest about their team and organizational preferences without the awkwardness of typical "culture fit" questions. Like most of these questions, there's no right or wrong answer—but the best answers demonstrate tight alignment with Almanac’s Virtues.

Question #7: What's the hardest you've ever worked on something and why did you care so much?

We look for people at Almanac who give a shit—who both care deeply about our mission and vision and more generally about whatever they are working on. So the only wrong answer to this question is to pause and not answer at all. I want to see someone light up and immediately tell me all about "this time when..." I want to feel their passion through the screen. I want to see if they have hunger and an intrinsic drive to succeed no matter how difficult the path.

Question #8: What's the last problem that kept you up all night?

As an early stage startup where success typically requires finding a new path over difficult obstacles, Almanac needs a team with endless curiosity who will not stop thinking about a problem until it's solved. Great answers here involve candidates convincingly talking about a work problem, not a life problem. I want to see just how deep curiosity runs in their veins.

Question #9: Why is Starbucks so successful?

At Almanac, structured thinking is our religion, and this is designed to test their ability to think, process, and present clearly. I want to see them take a problem, break it down into steps, and analyze each piece for validity.

Wrong answers include analyzing Starbucks as it is today—their stores are everywhere, or they're so consistent—versus how they got so big in the first place. Those are all outputs of their success, not inputs.

The awesome thing about Starbucks as a case is it shows you how different functional team members think. Great product managers wax poetic about the amazing user experience Starbucks created for their customers, turning a commodity into something special. Great marketers talk about how Starbucks created a new category for a "third place" between home and work and developed tactics that weaved Starbucks into everyday routines, like specific product naming conventions and their digital wallet. Great ops leads focus on Starbucks' brilliant real estate strategy across urban and suburban markets.

Question #10: Tell me about a product or service that other people think is bad, but that you think is great. Then, convince me I'm wrong.

First, I'm looking to make sure they listened to what I said. Most people just tell me what product is bad and they don't convince me of anything.

Then, I'm looking for candidates to empathize with why people might think it's bad in the first place. No one ever wins an argument—with teammates or customers—by telling them they're wrong.

Finally, I'm looking for them to share a new perspective on why it's great and overcome all of the existing objections with a convincing point of view and structured thinking

Question #11: How do you know if you're doing a good job in your role?

This is another way of asking "what do you think your job is?" A lot of startup roles have a high degree of ambiguity, and I'm looking to see if their definition of success matches with my definition.

Question #12: What's the best decision you made that was by all means unsuccessful?

There are many ways to be wrong and often few ways to be right, and success requires people analyzing their past decisions to understand where they made a wrong assumption, had a bias, or missed a clue.

In this question, I first look for candidates who feel comfortable addressing failure and admitting that they were wrong. I'm not looking for them to redeem the decision either by claiming that it led to other success down the road. I want to know if they can identify where they made an error , and then how they changed their approach so they don't make the same mistake twice. I want to see that they have a growth mindset–that they're always learning and aware of their own fallibility.

Question #13: What's something you did that nobody believed you could do?

I'm looking for persistence, drive, and grit. I'm less interested in personal things (like I ran a marathon or got into Harvard), and more interested in problems in the workplace. Like–my team didn't want me to build this but here's how I overcame their objections, won them to my side, and built it anyways.

Question #14: Why shouldn't we hire you?

I round out the interview by asking this. People are always thrown for a loop because of course they're trying to get hired! To be honest, sometimes people's answers reinforce doubts I've already formed during the interview—like they prefer structure or lots of direction, or they would rather run the company than be a part of it. However, if the worst a candidate can think of is not a disqualifier in my mind, they're all clear to move forward.

Question #15: If we were to hire you, how would you want to learn and grow while you're here?

Interviews are a two-way street—the candidate is evaluating us, and ultimately I want to understand how we can help them should they come work with us. I believe that in exchange for their work at Almanac, part of our compensation to our team is helping them learn and grow into the people they want to be. So, here I want an understanding of what they're looking for in their next job—what they're really looking for in their career. Based on their answer, I can also tailor my pitch to them down the road if we decide to extend an offer.

3 bonus tips for interviewing
        

Bonus Tip #1: Interviews are equal part evaluation and equal part selling.

It's important to use your time together to build a relationship, so be generous with your answers and thoughts. The candidate should get something out of the conversation, too, which is how you want your eventual relationship to be if they join your company.

Bonus Tip #2: Be as transparent as possible.

Share documentation with candidates ahead of time. Give them access to your company strategy, virtues, and other documentation. This makes the conversation more productive on a minute-by-minute basis, and saves you from answering questions you've already answered.

Here's a look at two of our internal docs that we share with our candidates ahead of time:

Q1 2022 Focuses password: focusisfun

Strategy 1H 2022 password: plg2022

Bonus Tip #3: Be kind.

People will often forget what you said, but they'll always remember how you made them feel.

so that's it.
        

Seven interview tips to keep in mind and 15 questions to ask in order to ignite your hiring process. If you liked these questions, check out some of the other questions I ask during interviews. You can find them here:

If you liked this piece on interviewing, follow me for more tips on how to build, scale, and run a startup. I talk about my experience and share my learnings along the way. You can find me:

On Twitter: adampnathan

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Hope to see you around!